V2753

Virginiamycin M₁

≥95% (HPLC)

• Synonym(s): Ostreogrycin A, Pristinamycin IIA, Staphylomycin M1, Streptogramin A, Virginiamycin M1, Mikamycin A, Staphylomycin
• Empirical Formula (Hill Notation): C₂₈H₃₅N₃O₇
• CAS Number: 21411-53-0
• Molecular Weight: 525.59
• EC Number: 244-376-6
• MDL number: MFCD00869411
• UNSPSC Code: 51283805
• PubChem Substance ID: 24900736
• NACRES: NA.85

Properties

• biological source: Streptomyces virginiae
• Quality Level: 200
• assay: ≥95% (HPLC)
• form: powder
• storage condition: (Keep container tightly closed in a dry and well-ventilated place.)
• color: white to yellow
• solubility: methanol: soluble 10 mg/mL
• antibiotic activity spectrum: Gram-positive bacteria
• mode of action: protein synthesis | interferes
• storage temp.: 2-8°C
• SMILES string: CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c3coc(CC(=O)C[C@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3
• InChI: 1S/C28H35N3O7/c1-17(2)26-19(4)9-10-24(34)29-11-5-7-18(3)13-20(32)14-21(33)15-25-30-22(16-37-25)27(35)31-12-6-8-23(31)28(36)38-26/h5,7-10,13,16-17,19-20,26,32H,6,11-12,14-15H2,1-4H3,(H,29,34)/b7-5-,10-9-,18-13-/t19-,20-,26-/m1/s1
• InChI key: DAIKHDNSXMZDCU-QHKJSJJMSA-N

Description

General description

Chemical structure: macrolide

Application

The antibiotic virginiamycin is produced by Streptomyces virginiae and is a member of the virginiamycin family. Each member is produced as a mixture of two structurally different compounds that exhibit synergistic antibacterial activity. There are two groups: virginiamycin M1 (VM1) and virginiamycin S (VS). VM1 is a polyunsaturated macrocyclic petolide. VM1 and VS are both used to inhibit protein synthesis since they are bacteriostatic. When used in combination they are more effective. Virginiamycin is used as a performance promoter in animal husbandry. They are chemically modified to make therapeutic drugs such as quinupristin and dalfopristin.

Biochem/physiol Actions

Virginiamycin M1 inhibits bacterial protein synthesis at the level of aminoacyl-tRNA binding and peptide bond formation. It inactivates the 50S ribosome. S. virginiae inactivates VM1 by reducing its 16-carbonyl group, forming 16R-dihydroVM1. VM1 reductase participates solely in VM1 inactivation in vivo.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)